After Smithers is crushed by Mr. Burns' lack of affection towards him, other characters attempt to find a boyfriend for him. Meanwhile, Milhouse competes against a new boy for the lead role in a school production of Casablanca, so he can act alongside his own unrequited love, Lisa.
- When Smithers and his new boyfriend are discussing travel plans, the scene cuts to a map and a dotted line goes from America to Cuba, suggesting they're already going there. It turns out they're still in Springfield and Smithers' boyfriend is just showing a planned route.
- When Smithers and his boyfriend get a license, it turns out to be a fishing license.
- Identical Stranger: Homer encounters a gay man who looks exactly like him, whom he promptly hires to impersonate him while visiting his father Abe.
- Reality Ensues: Smithers' substitute refuses to release the hounds on Lenny because it'd make her criminally responsible for what the hounds would do to him.